WO2005082967A1 - Hydrophobe, niedrigviskose polyole - Google Patents

Hydrophobe, niedrigviskose polyole Download PDF

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Publication number
WO2005082967A1
WO2005082967A1 PCT/EP2005/001488 EP2005001488W WO2005082967A1 WO 2005082967 A1 WO2005082967 A1 WO 2005082967A1 EP 2005001488 W EP2005001488 W EP 2005001488W WO 2005082967 A1 WO2005082967 A1 WO 2005082967A1
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WO
WIPO (PCT)
Prior art keywords
weight
polyols
hydrophobic polyols
viscosity
polyisocyanates
Prior art date
Application number
PCT/EP2005/001488
Other languages
German (de)
English (en)
French (fr)
Inventor
Meike Niesten
Jack Reese
Joachim Simon
Gerhard Ruttmann
Original Assignee
Bayer Materialscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Materialscience Ag filed Critical Bayer Materialscience Ag
Priority to PL05707388T priority Critical patent/PL1723187T3/pl
Priority to DE200550002292 priority patent/DE502005002292D1/de
Priority to BRPI0508189-0A priority patent/BRPI0508189A/pt
Priority to AU2005217046A priority patent/AU2005217046A1/en
Priority to UAA200610348A priority patent/UA84454C2/ru
Priority to EP05707388A priority patent/EP1723187B1/de
Priority to JP2007500101A priority patent/JP2007524746A/ja
Publication of WO2005082967A1 publication Critical patent/WO2005082967A1/de

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/487—Polyethers containing cyclic groups
    • C08G18/4879—Polyethers containing cyclic groups containing aromatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2150/00—Compositions for coatings
    • C08G2150/90—Compositions for anticorrosive coatings
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

  • the invention relates to novel hydrophobic, low-viscosity polyols, to a process for their preparation and to solvent-free binder mixtures based thereon, which are particularly suitable for primers of floor coatings.
  • Two-component solvent-free coating systems (2K systems) of the prior art are essentially composed of epoxy resin (2K-EP) systems and polyurethane (2K-PUR) systems.
  • Coatings based on 2-component EP systems combine good mechanical strength with high resistance to solvents and chemicals. In addition, they are characterized by a very good substrate adhesion. A significant disadvantage is their poor elasticity, especially at low temperatures. This brittleness leads to a poor crack bridging through the coating, so that an attack on the substrate can take place here. An additional disadvantage is the very low resistance to organic acids. This is especially problematic for applications in the food sector, as organic acids are often released as waste products.
  • a balanced combination of hardness and elasticity is the outstanding feature of 2K-PUR coatings and the biggest advantage over 2K-EP coatings.
  • the resistance to organic acids of 2K PUR coatings is significantly better than 2K EP coatings.
  • coating agents should be solvent-free, especially in thick film applications, such as floor coatings. This means that the intrinsic viscosity of the binder component should be low.
  • hydroxy-functional component is generally more hydrophilic than the polyisocyanate component, it is particularly important to use straight hydrophobic hydroxy-functional components.
  • the hydroxy-functional binder component of the 2K-PUR coating can be based on various chemical structure types. While polyester polyols are characterized by a low viscosity and relatively low water absorption, their saponification stability is low, which greatly limits their use for the corrosion protection of metallic substrates and for coating mineral (alkaline) substrates.
  • 2-component PUR coatings based on polyacrylate polyols are characterized by good resistance to saponification, but their relatively high viscosity level is disadvantageous. Therefore, either solvents or reactive diluents such as polyether polyols or polyfunctional alcohols are always added to adjust the viscosity. As is the case with the exclusive use of polyether polyols as crosslinkers, the water absorption behavior usually increases as a result.
  • Resins derived from cashew nut shell liquid are used in coatings and coatings (Shukia et al., In Paintindia, February 2002, pages 29-32, Nayak, Natural Oil-Based Polymers: Opportunities and Challenges, in JMS Rev. Macromol Chem. Phys., C40 (1), 12-18, 2000). Such products are very hydrophobic and, because of the absence of ester linkages, are stable to saponification.
  • CNSL based resins contain phenolic OH groups which can be used for crosslinking by reaction with polyisocyanates.
  • the disadvantage here is that the resulting phenol-based urethane bonds are not stable to backspin under moist, alkaline conditions.
  • J48-29530 describes the reaction of CNSL or cardanol aldehyde condensates with alkylene oxides such as propylene oxide, wherein the phenolic OH groups become aliphatically bonded hydroxyl groups.
  • alkylene oxides such as propylene oxide
  • the object of the present invention was therefore to provide a hydrophobic, low-viscosity polyol component which can be further processed into solvent-free binder mixtures and does not have the abovementioned disadvantages of the lack of resistance of the coatings based thereon, in particular in the area of thick-film applications. It has now been found that alkylene oxide adducts of cardanol-depleted CNSL of specific composition have the required polyol properties.
  • the invention relates to a process for preparing hydrophobic polyols having an OH number of 140 to 220 mg KOH / g and a viscosity at 23 ° C of 1 000 to 4 000 mPas, in which
  • alkylene oxides (AO) is reacted with addition of the AO monomers to the AO-reactive groups of component A),
  • ratio of the amounts of A) to B) is 1: 9 to 9: 1 and the amounts of Cardanol, Cardol and 6-methylcardol with the remaining constituents of component A) add up to 100 wt .-%.
  • polyols prepared by the process essential to the invention are an object of the present invention.
  • Cardanol (3-pentadecadienylphenol) is extracted from cashew nut shells or the CNSL contained therein.
  • the CNSL is extracted from the layer between nut and shell of the cashew nut.
  • This intermediate layer contains mainly anacardic acid (2-carboxy-3-pentadecadienylphenol) and related acids with different double-bond contents as well as Cardol (m-pentadecadienylresorcinol).
  • the liquid is extracted by heating from the intermediate layer, whereby the acids are decarboxylated.
  • the products thus obtained contain cardanol (I), Cardol (II) and related compounds with different numbers of double bonds.
  • a typical composition of such an extract is as follows:
  • the side chains which are saturated or cis-unsaturated, can further react by polymerization to higher molecular weight compounds ("polymer").
  • cardanol is isolated from CNSL by distillation.
  • the remaining residue in addition to higher molecular weight organic compounds, typically also contains 5 to 20% by weight of cardanol residues and 5 to 10% by weight of cardol (3-pentadecadienylresorcinol) and 1 to 5% by weight of 6-methylcardol (2-methyl-3-ol. pentadecadienylresorcinol).
  • such a residue is preferably used from cardanol production starting from cashew nut shell liquid (CNSL).
  • CNSL cashew nut shell liquid
  • this typically has from 60 to 80% by weight, preferably from 65 to 75% by weight, of optionally phenolic OH-functional organic compounds of a number average molecular weight M n > 700 g / mol , wherein the quantities of said constituents of the residue used add up to 100 wt .-%.
  • the mixture of component A) preferably has an OH content of 200 to 270 mg KOH / g.
  • the mixture of component A) preferably has a viscosity at 23 ° C. of from 5,000 to 20,000 mPas and preferably has an average OH functionality of from 3 to 4.
  • the ratio of the amounts of A) to B) is preferably 1: 5 to 5: 1.
  • component A) takes place by polyaddition of the compounds of component B) to groups of component A) having active hydrogen atoms.
  • alkylene oxides used are preferably ethylene oxide, propylene oxide, butylene oxide and mixtures thereof. When using two or more alkylene oxide types, these can be polyaddiert blockwise or randomly. For details, see “Ulimann's Encyclopedia of Industrial Chemistry", Vol. A21, 1992, p. 670f.
  • the polyaddition reaction can be carried out without catalyst or with the use of a catalyst.
  • a catalyst for this purpose, the compounds and catalyst systems known to the person skilled in the art, such as, for example, alkali metal hydroxides or double metal cyanide catalysts (DMC catalysts) are suitable.
  • DMC catalysts double metal cyanide catalysts
  • component A) is initially charged and mixed with component B) under polyaddition.
  • the process according to the invention is generally carried out at temperatures of from 20 to 200.degree. C., preferably from 40 to 180.degree. C., more preferably from 50 to 150.degree.
  • the reaction can be carried out at total pressures of 0.001 to 20 bar.
  • the polyaddition may be continuous or batch, e.g. be performed in a batch or semibatch process.
  • the polyols obtainable by the process according to the invention preferably have a viscosity at 23 ° C. of from 1,000 to 3,500 mPas and an OH number of from 150 to 220 mg KOH / g.
  • polyols according to the invention are distinguished by a particularly high hydrophobicity. They are therefore particularly suitable for the production of 2-component polyurethane coating systems (2-component PUR systems) for thick-film applications, for example in the construction sector.
  • PUR systems polyurethane systems (PUR systems), preferably 2K-PUR systems, at least containing
  • polyisocyanates of component b) typically organic polyisocyanates having an average NCO functionality of at least 2 and a molecular weight of at least 140 g / mol are used. Particularly suitable are, in particular, (i) unmodified organic polyisocyanates having a molecular weight range of 140 to 300 g / mol, (ii) coating polyisocyanates having a molecular weight in the range from 300 to 1000 g / mol and (iii) urethane group-containing NCO prepolymers of more than 1000 g / mol molecular weight lying or mixtures of (i) to (iii).
  • polyisocyanates of group (i) are 1,4-diisocyanatobutane, 1,6-diisocyanatohexane (HDI), 1,5-diisocyanato-2,2-dimethylpentane, 2,2,4- and 2,4,4- Trimethyl-l, 6-diisocyanatohexane, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), 1-isocyanato-1-methyl-4- (3) -isocyanatoxyethylcyclohexane, bis ( 4-isocyanatocyclohexyl) methane, 1,10-diisocyanatodecane, 1,12-diisocyanato-dodecane, cyclohexane-1,3- and -1,4-diisocyanate, xylylene diisocyanate isomers, triisocyanatononane (TIN), 2,
  • Polyisocyanates of group (ii) are the conventional lacquer polyisocyanates.
  • lacquer polyisocyanates is to be understood as meaning compounds or mixtures of compounds which are obtained by per se known oligomerization reaction of simple diisocyanates of the type mentioned under (i) by way of example.
  • Suitable oligomerization reactions are e.g. carbodiimidization, dimerization, trimerization, biuretization, urea formation, urethanization, allophanatization and / or cyclization to form oxadiazine structures. Often, in "oligomerization", several of the reactions mentioned occur simultaneously or in succession.
  • the "paint polyisocyanates” (ii) are preferably biuret polyisocyanates, isocyanurate-group-containing polyisocyanates, isocyanurate- and uretdione-group-containing polyisocyanate mixtures, urethane- and / or allophanate-group-containing polyisocyanates or isocyanurate- and allophanate-group-containing polyisocyanate mixtures simple diisocyanates.
  • Polyisocyanates of group (iii) are the isocyanate group-containing prepolymers based on simple diisocyanates of the type exemplified above and / or based on lacquer polyisocyanates (ii) on the one hand and organic polyhydroxy compounds of over 300 g / mol lying molecular weight on the other hand.
  • the urethane group-containing lacquer polyisocyanates of group (ii) are derivatives of low molecular weight polyols in the molecular weight range 62 to 300 g / mol (suitable polyols are, for example, ethylene glycol, propylene glycol, trimethylolpropane, glycerol or mixtures of these alcohols)
  • suitable polyols are, for example, ethylene glycol, propylene glycol, trimethylolpropane, glycerol or mixtures of these alcohols
  • Preparation of the NCO prepolymers of the group (iii) Polyhydroxylver- compounds having a molecular weight M n above 300 g / mol, preferably above 500 g / mol, particularly preferably from 500 to 8000 g / mol used.
  • Such polyhydroxyl compounds are, in particular, those which have 2 to 6, preferably 2 to 3, hydroxyl groups per molecule and are selected from the group consisting of ether, ester, thioether, carbonate and polyacrylate polyols and mixtures of such polyols.
  • said higher molecular weight polyols can also be used in blends with said low molecular weight polyols, so that directly mixtures of low molecular weight urethane containing paint polyisocyanates (ii) and higher molecular weight NCO prepolymers (iii) result.
  • diisocyanates (i) of the type exemplified above or lacquer polyisocynatates of the type exemplified under (ii) with the higher molecular weight hydroxyl compounds or mixtures thereof with low molecular weight polyhydroxy compounds are exemplified mentioned type while maintaining an NCO / OH equivalent ratio of 1.1: 1 to 40: 1, preferably 2: 1 to 25: 1 reacted with urethane formation.
  • an excess of distillable starting diisocyanate it may be removed by distillation following the reaction so that monomer-free NCO prepolymers, i. Mixtures of starting diisocyanates (i) and true NCO prepolymers (iii).
  • the said polyisocyanates are used in unblocked form, so that 2K-PUR systems are obtained.
  • blocking agents it is also possible to use blocking agents to block the NCO groups of the abovementioned polyisocyanates, so that they can be formulated with the essential polyols to give storage-stable IK-PUR systems.
  • the amounts of components a), b) and optionally other constituents are chosen so that an NGO: OH equivalent ratio of 0.5: 1 to 2.0: 1, preferably 0.8: 1 to 1.5: 1 results.
  • further constituents such as additional higher or low molecular weight polyols, catalysts or auxiliaries and additives may be present in the PU systems according to the invention.
  • the compounds known per se in polyurethane chemistry can be used to accelerate the NCO / OH reaction (cf "Kunststoff Handbuch 7, Polyurethane” Carl-Hanser-Verlag, Kunststoff-Vienna, 1984, pp. 97-98 ).
  • tertiary amines such as triethylamine, pyridine, methylpyridine, benzyldimethylamine, N, N-endoethylenepiperazine, N-methylpiperidine, pentamethyldiethylenetriamine, N, N-dimethylaminocyclohexane, N, N'-dimethylpiperazine or metal salts such as iron (IH) chloride, zinc chloride, zinc 2-ethylcaproate, stannous octoate, Znn (H) -ethylcaproate, tin (H) -palmitate, dibutyltin (IV) dilaurate and molybdenum glycolate or any mixtures of such catalysts.
  • Preferred compounds of component C) are tin compounds.
  • auxiliaries or additives in the PUR systems for example, surface-active substances, internal release agents, fillers, dyes, pigments, flame retardants, hydrolysis protectants, microbicides, flow control agents, antioxidants such as 2,6-di-tert-butyl-4-methylphenol , UV absorber of the type 2-hydroxyphenyl-benzotriazole or light stabilizers of the type substituted on the nitrogen atom or unsubstituted HALS compounds such as Tinuvin ® 292 and Tinuvin ® 770 DF (Ciba specialties GmbH, Lampertheim, DE) or other commercially available stabilizers, such as in "light stabilizers for paints" (A. Valet, Vincentz Verlag, Hannover, 1996 and “Stabilization of Polymeric Materials” (H. Zweifel, Springer Verlag, Berlin, 1997, Appendix 3, pp. 181-213) are used ,
  • the components a), b) and, if appropriate, further crosslinker components are mixed with one another such that an NCO: OH equivalent ratio of 0.5: 1 to 2.0: 1, preferably 0 , 8: 1 to 1.5: 1 results.
  • the auxiliaries and additives mentioned and also catalysts can be added.
  • the application of the PUR systems according to the invention can be carried out by methods customary per se in the art, such as brushing, knife coating, spraying, dipping.
  • the PU systems of the invention are characterized by their only very low water absorption of preferably less than 7 wt .-%, particularly preferably less than 4 wt .-%.
  • Preferred layer thicknesses are from 0.5 to 10 mm, preferably from 0.7 to 6 mm, whereby the production of thinner or thicker layers is not excluded.
  • PUR systems In principle, all kinds of materials can be coated with the PUR systems according to the invention. Examples include glass, wood, metal, mineral substrates such as concrete.
  • the PUR systems are preferably used for the production of coatings for the protection of metallic substrates against mechanical damage and corrosion and for the protection of mineral substrates, such as concrete, against environmental influences and mechanical damage.
  • the dynamic viscosities were determined according to DIN 53019 at 23 ° C. using a rotational viscometer (Viscotester 550, Thermo Hakke GmbH, D-76227 Düsseldorf) at a shear rate of 40 s -1 .
  • the Shore D hardness was determined according to DUST 53505.
  • Water uptake was determined by weight gain from a sample after 21 days of open storage at 23 ° C and 97% humidity.
  • the water absorption is calculated according to the following formula:
  • the polyol component was mixed with the polyisocyanate component in an NCO / OH ratio of 1: 1 and applied to a plastic substrate by means of casting in a layer thickness of 3 to 5 mm. The subsequent curing took place at room temperature.
  • composition (% by weight) 1 2 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyethers (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/EP2005/001488 2004-02-28 2005-02-15 Hydrophobe, niedrigviskose polyole WO2005082967A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
PL05707388T PL1723187T3 (pl) 2004-02-28 2005-02-15 Hydrofobowe poliole o małej lepkości
DE200550002292 DE502005002292D1 (de) 2004-02-28 2005-02-15 Hydrophobe, niedrigviskose polyole
BRPI0508189-0A BRPI0508189A (pt) 2004-02-28 2005-02-15 polióis hidrófobos de baixa viscosidade
AU2005217046A AU2005217046A1 (en) 2004-02-28 2005-02-15 Hydrophobic low-viscous polyols
UAA200610348A UA84454C2 (ru) 2004-02-28 2005-02-15 Способ получения гидрофобных полиолов и полиуретановые системы, которые их содержат
EP05707388A EP1723187B1 (de) 2004-02-28 2005-02-15 Hydrophobe, niedrigviskose polyole
JP2007500101A JP2007524746A (ja) 2004-02-28 2005-02-15 低粘度疎水性ポリオール

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004009818.2 2004-02-28
DE200410009818 DE102004009818A1 (de) 2004-02-28 2004-02-28 Hydrophobe, niedrigviskose Polyole

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WO2005082967A1 true WO2005082967A1 (de) 2005-09-09

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US (1) US7393465B2 (enrdf_load_stackoverflow)
EP (1) EP1723187B1 (enrdf_load_stackoverflow)
JP (1) JP2007524746A (enrdf_load_stackoverflow)
KR (1) KR20060133591A (enrdf_load_stackoverflow)
CN (1) CN100471891C (enrdf_load_stackoverflow)
AT (1) ATE381581T1 (enrdf_load_stackoverflow)
AU (1) AU2005217046A1 (enrdf_load_stackoverflow)
BR (1) BRPI0508189A (enrdf_load_stackoverflow)
DE (2) DE102004009818A1 (enrdf_load_stackoverflow)
ES (1) ES2297670T3 (enrdf_load_stackoverflow)
PL (1) PL1723187T3 (enrdf_load_stackoverflow)
RU (1) RU2006134266A (enrdf_load_stackoverflow)
UA (1) UA84454C2 (enrdf_load_stackoverflow)
WO (1) WO2005082967A1 (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006037288A1 (de) * 2006-08-09 2008-02-14 Ashland-Südchemie-Kernfest GmbH Verwendung von Cashew-Nutshell Derivaten in Gießereibindemitteln aus Polyurethanbasis

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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CN1926165A (zh) 2007-03-07
CN100471891C (zh) 2009-03-25
DE502005002292D1 (de) 2008-01-31
DE102004009818A1 (de) 2005-09-15
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US7393465B2 (en) 2008-07-01
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